Manufacture of aromatic amino sulphocyano derivatives



Patented Oct. 16, 1928.

I UNITED STATES PATENTOFl-ICE.

l OSKAR SPENGLER, 0F DESSAU IN ANHALT AND WERNER MiiLLEn, or LEIPZIG, ena- MANY, ASSIGNORS TO GRASSELLI DYESTUFF CORPORATION, OF NEW YORK, N. Y., A

CORPORATION OF DELAWARE.

MANUFACTURE OF AROMATIC AMINO SULPHOCYANO DERIVATIVES.

24, 1924. Divided and this application In an application Ser'. No. 54,131, filed Sept. 2, 1.925, and granted as U. S. Patent 1,594,697, We claim the manufacture of sulphocyano derivatives by causing a solution containing a product of the reaction between a halide of sulphuric acid and a sulphocyanide to react with a hydroxyaryl compound.

Nowin the present invention which is a division of the above mentioned application we claim the manufacture of sulphocyano derivatives by causing a solution containing a product of the reaction between a halide of sulphuric acid and a sulphocyanide to react with an, aminoaryl compound. The reaction in a suitable solvent between a halide of sulphuric acid and a su'l hocyanide, for example, lead 'sulphocyani e, produces a solution containing a compound which easily decomposes into 'thiocyanogen and sulphurous acid. One can assume the production of a sulphuryl sulphocyanide as an intermediate stage in the reaction between'a sulphocyanide and a sulphochloride .for example.

The following example illustrates the invention, the parts being by weight: 13.5 parts of sulphurylchloride are dissolved in 400 parts of carbon tetrachloride and an excess of fineliy powdered lead sulpho-v cyanide is introduce A lively reaction sets in at once and after some time the reaction is completed. The leadchloride and excess of sulphocyanide are separated by filtration and the filtrate mixed with a cold solution of 8.5

a No Drawing. Original application filed September 2, 1925, Serial No 54,131, and in Germany September filed April 28, 1926. Serial No 105,260.

parts of diphenylamine in chloroform. Hydrogen sulphocyanide is rapidl evolved and the solution becomes turbid, a brown oil separating from it; this oil becomes crystalline when rubbed with a glass-rod. On recrystallization there is obtained the 4.4-disulphgcyano diphenylamine of melting point 120 It is obvious to those skilled in the art that our present invention is not limited to the foregoing example or to the details given therein. It may be stated for instance that instead of the diphenylamine employed in the foregoing example any aminoaryl compound may be used. It is obvious that in em'-' ploying such other aminoaryl compound the proportions of the ingredients as Well asthe other special conditionsof reaction may be altered in order to obtain the best results Having now described our invention and the manner in which it may be carried out what we claim is,-

The herein described manufacture of sulphocyano derivatives by causing a solution containing a product of the reaction between a halide of sulphuric acid and a sulphocyanide to react with aromatic amino com- 60 pounds.

In testimony whereof we afiix our signatures..

OSKAR SPENGLER. WERNER MULLER. 

